Palladium-mediated cyclization of 6-methyl-1-phenyl-6-hepten-2-one to form 3-methyldiphenylmethane: Carbonyl activation by a neutral palladium(II) complex
Publication
, Journal Article
Han, X; Widenhoefer, RA
Published in: Organometallics
July 30, 2007
Reaction of 6-methyl-1-phenyl-6-hepten-2-one (4) with a stoichiometric mixture of PdCl 2(CH 3CN) 2 (2) and Me 3SiCl in dioxane at 70 °C formed 3-methyldiphenylmethane (6) in 78% isolated yield. A number of experiments supported a mechanism for the conversion of 4 to 6 initiated by palladium-mediated carbonyl-ene reaction to form the isolable palladium alkene-alcohol complex Pd[η 3-HOC(Bn) CH 2C(Me)=CHCH 2CH 2]Cl 2 (7) followed by Me 3SiCl-mediated dehydration to form the unobserved palladium diene complex Pd[η 4-C(Bn)=C(Me)CH=CHCH 2CH 2]Cl 2 (II) and palladium-mediated oxidation of II to form 6. © 2007 American Chemical Society.
Duke Scholars
Published In
Organometallics
DOI
ISSN
0276-7333
Publication Date
July 30, 2007
Volume
26
Issue
16
Start / End Page
4061 / 4065
Related Subject Headings
- Organic Chemistry
- 3406 Physical chemistry
- 3402 Inorganic chemistry
- 0399 Other Chemical Sciences
- 0305 Organic Chemistry
- 0302 Inorganic Chemistry
Citation
APA
Chicago
ICMJE
MLA
NLM
Han, X., & Widenhoefer, R. A. (2007). Palladium-mediated cyclization of 6-methyl-1-phenyl-6-hepten-2-one to form 3-methyldiphenylmethane: Carbonyl activation by a neutral palladium(II) complex. Organometallics, 26(16), 4061–4065. https://doi.org/10.1021/om700379g
Han, X., and R. A. Widenhoefer. “Palladium-mediated cyclization of 6-methyl-1-phenyl-6-hepten-2-one to form 3-methyldiphenylmethane: Carbonyl activation by a neutral palladium(II) complex.” Organometallics 26, no. 16 (July 30, 2007): 4061–65. https://doi.org/10.1021/om700379g.
Han X, Widenhoefer RA. Palladium-mediated cyclization of 6-methyl-1-phenyl-6-hepten-2-one to form 3-methyldiphenylmethane: Carbonyl activation by a neutral palladium(II) complex. Organometallics. 2007 Jul 30;26(16):4061–5.
Han, X., and R. A. Widenhoefer. “Palladium-mediated cyclization of 6-methyl-1-phenyl-6-hepten-2-one to form 3-methyldiphenylmethane: Carbonyl activation by a neutral palladium(II) complex.” Organometallics, vol. 26, no. 16, July 2007, pp. 4061–65. Scopus, doi:10.1021/om700379g.
Han X, Widenhoefer RA. Palladium-mediated cyclization of 6-methyl-1-phenyl-6-hepten-2-one to form 3-methyldiphenylmethane: Carbonyl activation by a neutral palladium(II) complex. Organometallics. 2007 Jul 30;26(16):4061–4065.
Published In
Organometallics
DOI
ISSN
0276-7333
Publication Date
July 30, 2007
Volume
26
Issue
16
Start / End Page
4061 / 4065
Related Subject Headings
- Organic Chemistry
- 3406 Physical chemistry
- 3402 Inorganic chemistry
- 0399 Other Chemical Sciences
- 0305 Organic Chemistry
- 0302 Inorganic Chemistry